1,8-Diazabicyclo(5.4.0)undec-7-ene → Ethyl 6-fluoro-1-methyl-4-oxo-7-(3-trifluoroacetylamino-1-pyrrolidinyl)-1H,4H-[1,3]thiazeto[3,2-a]quinoline-3-carboxylate

HRID 893575Notes

Reaction equation

HRID 893575 reaction equation
[F:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][C:11]=1F)[N:8]1[CH:13]([CH3:15])[S:14][C:7]1=[C:6]([C:16]([O:18][CH2:19][CH3:20])=[O:17])[C:5]2=[O:21].Cl.[F:23][C:24]([F:34])([F:33])[C:25]([NH:27][CH:28]1[CH2:32][CH2:31][NH:30][CH2:29]1)=[O:26].C1CCN2C(=NCCC2)CC1>CN(C)C=O>[F:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][C:11]=1[N:30]1[CH2:31][CH2:32][CH:28]([NH:27][C:25](=[O:26])[C:24]([F:34])([F:33])[F:23])[CH2:29]1)[N:8]1[CH:13]([CH3:15])[S:14][C:7]1=[C:6]([C:16]([O:18][CH2:19][CH3:20])=[O:17])[C:5]2=[O:21]

Participants

5

Reactant 3

HCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 27606983-(Trifluoroacetamido)pyrrolidine HydrochlorideHCID 10380740Ethyl 6,7-difluoro-1-methyl-4-oxo-1,4-dihydro-[1,3]thiazeto[3,2-a]quinoline-3-carboxylate

Product 1

HCID 19890700Ethyl 6-fluoro-1-methyl-4-oxo-7-(3-trifluoroacetylamino-1-pyrrolidinyl)-1H,4H-[1,3]thiazeto[3,2-a]quinoline-3-carboxylateYield 80.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 1.00 g of ethyl 6,7-difluoro-1-methyl-4-oxo-1H,4H-[1,3]thiazeto[3,2-a]quinoline-3-carboxylate, 2.1 g of 3-trifluoroacetylaminopyrrolidine hydrochloride, 1.46 g of 1,8-diazabicyclo[5,4,0]-7-undecene and 20 ml of N,N-dimethylformamide was stirred at room temperature for 72 hours. The reaction mixture was concentrated in vacuo, and, to a suspension of the residue in 20 ml of methanol, 30 ml of water was added. The precipitate was collected by filtration to give 1.22 g of the desired compound, which was recrystallized from a mixture of chloroform and ethanol to give colorless crystals, m.p. 255°-257° C. (decomp.).

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. additionto a suspension of the residue in 20 ml of methanol
  3. addition30 ml of water was added
  4. filtrationThe precipitate was collected by filtration

Sources & evidence

ORD record
ord-2aef8a48484544f0bcab37138328fd1a
Source dataset
uspto-grants-1992_06
Patent number
US05126337

Reaction notes

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